[chrisbolt]

By default, iTunes pops up a message saying "you have purchased items on this device, would you like to transfer them?"

It sounds like your co-worker said no to this in the past, and checked the box to not pop up the message anymore.

[S_A_P]

I think that is kind of the point. It isn't really immediately clear what that will do. I think the message should read something to the effect of "You have purchased items on your device, which are not currently sync'ed to this computer. Would you like to transfer them now?"